Triethylamine → 5-(3-Methoxyphenyl)benzimidazolidin-2-one

HRID 496264Notes

Reaction equation

HRID 496264 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([NH2:18])=[C:13]([CH:17]=2)C(O)=O)[CH:6]=[CH:7][CH:8]=1.C[N:20]1CCC[C:21]1=[O:25].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[NH:18][C:21](=[O:25])[NH:20][C:13]=3[CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 223253354-Amino-3'-methoxy[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 223253275-(3-Methoxyphenyl)benzimidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 5-(3-methoxyphenyl)-2-aminobenzoic acid (2.0 g) in 1,4-dioxane (20 mL) add N-methylpyrolidinone (NMP, 5 mL) and triethylamine (1.4 mL), followed by diphenyl phosphoric azide (DPPA, 2.5 g). After stirring at ambient temperature for 30 minutes, heat the mixture to 100° C. for 2 hours, until gas evolution fully subsided. Cool the mixture to ambient temperature and concentrate in vacuo. Dissolve the residue in MeOH and leave to stand for 18 hours. Filter the precipitate and air dry to obtain 5-(3-methoxyphenyl)benzimidazolidin-2-one as a pale yellow solid. C. 2-Chloro-5-(3-methoxyphenyl)benzimidazole

Workup

  1. temperatureheat the mixture to 100° C. for 2 hours
  2. temperatureCool the mixture to ambient temperature
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in MeOH
  5. customleave
  6. waitto stand for 18 hours
  7. filtrationFilter the precipitate and air
  8. customdry

Sources & evidence

ORD record
ord-425a36a3b72d40c290f45ea2896389c4
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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